The purpose of this review is to examine the recent literature concerning the role of dairy fat intake on cardiometabolic health, focusing on prospective cohort studies that evaluated associations between dairy fat intake and cardiovascular disease (CVD) and type 2 diabetes (T2D). In general, studies using self-reported dietary assessment methods found no association between self-reported high-fat or low-fat dairy intake and CVD, a neutral association between low-fat dairy intake and incident of T2D, and either a protective association or no association between high-fat dairy intake and incident of T2D. Inconsistent classification of dairy foods as low- or high-fat and variable adjustment for potential confounders may have contributed to the heterogeneity of results. In contrast, results from studies using pentadecanoic acid (15:0), heptadecanoic acid (17:0), or trans-palmitoleic acid (t-16:1n-7) as biomarkers have provided consistent evidence that dairy fat intake was negatively associated with CVD and T2D risk. Taken together, results from prospective studies do not support the assumption that higher dairy fat intake is associated with increased risk of CVD, but they do support the hypothesis that dairy fat intake could be protective for T2D. Randomized controlled trials are needed to establish a cause-and-effect relationship between dairy fat intake and cardiometabolic disease risk.